To Play Transgender, Sandra Caldwell Had to Open Up About Who She Is

Sandra Caldwell talking with Will Davis, her director in the play “Charm.”Credit
Da Ping Luo

It wasn’t Sandra Caldwell’s first audition. By the time she came in to read for the part of Mama Darleena in Philip Dawkins’s drama “Charm,” Ms. Caldwell had been in dozens of films, television shows, musicals and plays. She’d performed at the Moulin Rouge in Paris, played a small part in Maya Angelou’s “Down in the Delta” and had a role in the BET mini-series “The Book of Negroes.”

But she was shaking when it was time to read for a part for “Charm,” an MCC Theater production that begins previews performances Off Broadway on Thursday.

“My soul was jumping out the window,” she said recently. She smiled broadly and shook her head as she retold the story. “I had no idea what was going to happen.”

It wasn’t her first audition, but it was her first time auditioning as an openly transgender woman. And she was reading for a role that tracked so closely with her personal narrative, she said, that “the monologue in the middle, I could have taken her name off and put my name in.”

Like her, Mama Darleena — based on a real person named Gloria Allen — is a black transgender woman in her 60s. Unlike her, Mama Darleena had been openly trans-identifying since her transition. At 65, Ms. Caldwell was ready to open up.

The show’s casting director, Adam Caldwell, could tell she was nervous. (They are not related.) But he was struck by her energy and charisma, and how exactly she matched the description of the character. He and MCC had been struggling to cast the part for months.

He sent a message to William Cantler, an artistic director of the theater: “I think you should come to Studio 6.” Mr. Cantler did. After a work session with the director, Will Davis, and a callback — in which, Mr. Cantler said, Ms. Caldwell “took control of that room” — they offered her the part. She burst into tears. So did Mr. Dawkins.

Now in rehearsal, Ms. Caldwell has largely worked through those initial nerves. Her stage presence is powerful: On a recent afternoon, after a successful run-through of a tense early scene, she did a full-body dance around the perimeter of the room, then pumped a fist.

Photo

Left, Mr. Davis, the director of “Charm” and right, Philip Dawkins, its playwright. Center, Gloria Allen, the inspiration for the play’s lead character.Credit
Da Ping Luo

“She’s working so hard,” Mr. Davis said. “She really wants to get this right.”

“Charm” follows a crew of teenagers and 20-somethings from wildly different backgrounds who attend etiquette classes at an L.G.B.T.Q. youth center in Chicago, taught by Mama Darleena. Many of the characters are transgender, and Mr. Davis, who is trans-identifying, felt strongly that the parts went to people whose gender identities matched the roles.

In a theater world where jobs still remain heavily white and male, it is not surprising that parts for trans-identifying actors are limited. In his experience, Mr. Davis said, theaters often give familiar reasons for not casting actors from historically marginalized groups: “The same two things get said: ‘One, I can’t find them; two, they’re not trained.’ So I feel very, very strongly that it’s actually the responsibility of the institution to find and train them.”

MCC used nontraditional methods to find actors for the nine-member cast. They put out a call on social media, tried networking through friends, and reached out to lesbian and gay youth centers and organizations. They tried to cast a net well beyond New York City and Los Angeles.

Mama Darleena was a particular challenge. “The fact that a trans woman of color in her 60s is alive is a miracle in and of itself because of the oppressive ways that that group of people has been treated in the last 60 years,” Mr. Davis said. “The idea that then on top of that, that person was an actor was a really tall order.”

In the 2015 world premiere of “Charm” in Chicago, Mama Darleena was played by a cisgender, or gender conforming, man — though in three other productions, she has been played by transgender women.

Ms. Caldwell was born in Washington but ran away to New York several times, beginning when she was 13 — her way, she said, of “figuring things out.” When she was 18, she bought a $6 ticket to a Broadway show. “I didn’t know what it was, I just saw the lights,” Ms. Caldwell said. It turned out to be the Stephen Sondheim musical “Follies,” starring the original cast. “I knew right then that this was what I wanted to do,” she said.

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She completed her transition around the age of 19. Her mother, with the help of two friends who were involved with L.G.B.T.Q. issues, brought her to counseling and psychiatrists before she received hormone therapy. Afterward, Ms. Caldwell said, “I felt a lot of joy, and also relief.”

“Back then,” she added “the rules were, you did what you had to do and kept your mouth shut.” Outside of her family, only a small group of friends from Washington who had known her as a child were aware of her transition.

She auditioned for a role as showgirl in New York — and ultimately traveled to Europe and worked at the Moulin Rouge. She had success as an actress. She wrote a one-woman show seven years ago about her life and travels, “The Guide to Being Fabulous After You’ve Skinned Your Knee,” and performed it at Berkeley Street Theater in Toronto, where she lived for over a decade.

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At 65, Ms. Caldwell has begun to reveal that she is transgender. She’s playing a character who’s very similar to her in “Charm.”Credit
Tony Cenicola/The New York Times

But she never mentioned her transition. After that show, “the bottom fell out because I felt like I was lying,” she said. “I had left myself out. I left the truth about me out.”

Eventually, Ms. Caldwell said, she came to a conclusion: She wanted to start sharing that truth with the world.

About a year ago, she approached Alicia Jeffery, her manager of 14 years. Ms. Caldwell confessed to her that she had transitioned many years ago and was ready to share that with the world.

“I had absolutely no idea,” Ms. Jeffery said. “She was known around Toronto to be this very foxy, sexy actress and singer. Which is what she is.” They discussed how she might rework her one-woman play to include her transition, and how she might begin to share her story publicly.

Shortly after, Ms. Jeffery saw a casting call for “Charm,” and the description of Mama Darleena. She asked Ms. Caldwell if she wanted to be submitted for the part, and Ms. Caldwell said yes. “Well, here we go,” Ms. Caldwell recalled saying.

Ms. Caldwell said that she was drawn to the play partly because it wasn’t a tragedy. “Some movies with a trans theme — not so much anymore — but they always used to start with somebody being beat up,” she said. “Or somebody being hurt. This has nothing to do with that whatsoever. All it touches is this woman who has a gift, a skill to help these folks along.”

Ms. Allen, on whom the Mama Darleena character is based, is 72 and still lives in Chicago. She no longer teaches etiquette classes, but she recently flew to New York to meet the cast of “Charm.”

Of Ms. Caldwell, she said, “I met her and I fell in love with her right then and there because she is so down to earth and so classy, and I said ‘O.K., I see myself in her.’” They’ve become friends.

Ms. Caldwell knows that once the play opens on Sept. 18, much more may change for her. This is the first time she is sharing the story of her transition in an interview.

“I don’t know what it’s going to be like,” she said. “But I kind of want to live the rest of what I’ve got on this planet as if there’s such a thing as complete freedom. I want to live in that.”

A version of this article appears in print on August 29, 2017, on Page C1 of the New York edition with the headline: At 65, Finding Freedom Through a Stranger’s Story. Order Reprints|Today's Paper|Subscribe